CN1138818C - Polyamideimide for optical communications and method for preparing the same - Google Patents
Polyamideimide for optical communications and method for preparing the same Download PDFInfo
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- CN1138818C CN1138818C CNB981117937A CN98111793A CN1138818C CN 1138818 C CN1138818 C CN 1138818C CN B981117937 A CNB981117937 A CN B981117937A CN 98111793 A CN98111793 A CN 98111793A CN 1138818 C CN1138818 C CN 1138818C
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- 230000003287 optical effect Effects 0.000 title claims abstract description 33
- 238000000034 method Methods 0.000 title claims abstract description 26
- 238000004891 communication Methods 0.000 title claims abstract description 21
- 239000004962 Polyamide-imide Substances 0.000 title claims abstract description 17
- 229920002312 polyamide-imide Polymers 0.000 title claims abstract description 17
- 239000011541 reaction mixture Substances 0.000 claims description 102
- -1 diamine compound Chemical class 0.000 claims description 66
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 65
- 239000012153 distilled water Substances 0.000 claims description 64
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 46
- 238000006243 chemical reaction Methods 0.000 claims description 45
- 125000005843 halogen group Chemical group 0.000 claims description 35
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- 229910052731 fluorine Inorganic materials 0.000 claims description 17
- 239000011737 fluorine Substances 0.000 claims description 17
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 14
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 239000000178 monomer Substances 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 8
- 150000002367 halogens Chemical class 0.000 claims 7
- 229920005575 poly(amic acid) Polymers 0.000 claims 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 2
- 230000009477 glass transition Effects 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
- 238000005979 thermal decomposition reaction Methods 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 15
- 230000031700 light absorption Effects 0.000 abstract description 4
- 239000011248 coating agent Substances 0.000 abstract description 3
- 238000000576 coating method Methods 0.000 abstract description 3
- 239000013307 optical fiber Substances 0.000 abstract description 2
- 239000000758 substrate Substances 0.000 abstract description 2
- 238000005253 cladding Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 43
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 32
- 238000001291 vacuum drying Methods 0.000 description 29
- 230000015572 biosynthetic process Effects 0.000 description 27
- SXTAUSJLLADWLQ-UHFFFAOYSA-N 8-benzyl-2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5h-isoquinolino[2,1-b]isoquinoline Chemical compound C1=CC(OC)=C(OC)C2=C1CC1C=3C=C(OC)C(OC)=CC=3CCN1C2CC1=CC=CC=C1 SXTAUSJLLADWLQ-UHFFFAOYSA-N 0.000 description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- 239000004642 Polyimide Substances 0.000 description 18
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 18
- 229920001721 polyimide Polymers 0.000 description 18
- 239000002904 solvent Substances 0.000 description 14
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- RFCSBSYVCMPSOR-UHFFFAOYSA-N C1=CC(=C(C2=C1C(=O)NC2=O)Cl)C(=O)Cl Chemical compound C1=CC(=C(C2=C1C(=O)NC2=O)Cl)C(=O)Cl RFCSBSYVCMPSOR-UHFFFAOYSA-N 0.000 description 12
- XCJXQCUJXDUNDN-UHFFFAOYSA-N chlordene Chemical compound C12C=CCC2C2(Cl)C(Cl)=C(Cl)C1(Cl)C2(Cl)Cl XCJXQCUJXDUNDN-UHFFFAOYSA-N 0.000 description 12
- 238000001035 drying Methods 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 239000002253 acid Substances 0.000 description 11
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 9
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 9
- 239000001294 propane Substances 0.000 description 9
- 239000004215 Carbon black (E152) Substances 0.000 description 8
- 229930195733 hydrocarbon Natural products 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 description 6
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- IVHRXFBIIZXYCI-UHFFFAOYSA-N 3-n-fluorobenzene-1,3-diamine Chemical compound NC1=CC=CC(NF)=C1 IVHRXFBIIZXYCI-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 238000005660 chlorination reaction Methods 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 4
- 229940044174 4-phenylenediamine Drugs 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical group C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 4
- 238000001311 chemical methods and process Methods 0.000 description 4
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 4
- LFQKIPWZIYUJLP-UHFFFAOYSA-N 2-n-fluorobenzene-1,2-diamine Chemical compound NC1=CC=CC=C1NF LFQKIPWZIYUJLP-UHFFFAOYSA-N 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 239000011247 coating layer Substances 0.000 description 3
- 239000011162 core material Substances 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 239000012286 potassium permanganate Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- SOZFIIXUNAKEJP-UHFFFAOYSA-N 1,2,3,4-tetrafluorobenzene Chemical compound FC1=CC=C(F)C(F)=C1F SOZFIIXUNAKEJP-UHFFFAOYSA-N 0.000 description 2
- CPHXLFKIUVVIOQ-UHFFFAOYSA-N 2-(trifluoromethoxy)benzaldehyde Chemical group FC(F)(F)OC1=CC=CC=C1C=O CPHXLFKIUVVIOQ-UHFFFAOYSA-N 0.000 description 2
- PEODRFVJTWLUPF-UHFFFAOYSA-N 3-(3-amino-2,4,5,6-tetrafluorophenyl)-2,4,5,6-tetrafluoroaniline Chemical group NC1=C(F)C(F)=C(F)C(C=2C(=C(F)C(F)=C(N)C=2F)F)=C1F PEODRFVJTWLUPF-UHFFFAOYSA-N 0.000 description 2
- FWOLORXQTIGHFX-UHFFFAOYSA-N 4-(4-amino-2,3,5,6-tetrafluorophenyl)-2,3,5,6-tetrafluoroaniline Chemical group FC1=C(F)C(N)=C(F)C(F)=C1C1=C(F)C(F)=C(N)C(F)=C1F FWOLORXQTIGHFX-UHFFFAOYSA-N 0.000 description 2
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical class C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 2
- AZSDEGXYYBHUKM-UHFFFAOYSA-N 4-n-fluorobenzene-1,4-diamine Chemical compound NC1=CC=C(NF)C=C1 AZSDEGXYYBHUKM-UHFFFAOYSA-N 0.000 description 2
- OAPDPORYXWQVJE-UHFFFAOYSA-N 4-propylaniline Chemical compound CCCC1=CC=C(N)C=C1 OAPDPORYXWQVJE-UHFFFAOYSA-N 0.000 description 2
- 125000006414 CCl Chemical group ClC* 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-VVKOMZTBSA-N Dideuterium Chemical compound [2H][2H] UFHFLCQGNIYNRP-VVKOMZTBSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 230000010748 Photoabsorption Effects 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- SYHPANJAVIEQQL-UHFFFAOYSA-N dicarboxy carbonate Chemical compound OC(=O)OC(=O)OC(O)=O SYHPANJAVIEQQL-UHFFFAOYSA-N 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 125000004438 haloalkoxy group Chemical group 0.000 description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 2
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000005693 optoelectronics Effects 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000013308 plastic optical fiber Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- 238000001149 thermolysis Methods 0.000 description 2
- 150000003568 thioethers Chemical class 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- IOSNGZNEHBUCAR-UHFFFAOYSA-N (3-amino-2,4,5,6-tetrafluorophenyl)-(4-amino-2,3,5,6-tetrafluorophenyl)methanone Chemical compound FC1=C(F)C(N)=C(F)C(F)=C1C(=O)C1=C(F)C(N)=C(F)C(F)=C1F IOSNGZNEHBUCAR-UHFFFAOYSA-N 0.000 description 1
- QYAPHLRPFNSDNH-MRFRVZCGSA-N (4s,4as,5as,6s,12ar)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide;hydrochloride Chemical compound Cl.C1=CC(Cl)=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]4(O)C(=O)C3=C(O)C2=C1O QYAPHLRPFNSDNH-MRFRVZCGSA-N 0.000 description 1
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 1
- QJHMHZVVRVXKOY-UHFFFAOYSA-N 1,2,3,4,5-pentafluoro-6-(2,3,4,5,6-pentafluorophenoxy)benzene Chemical class FC1=C(F)C(F)=C(F)C(F)=C1OC1=C(F)C(F)=C(F)C(F)=C1F QJHMHZVVRVXKOY-UHFFFAOYSA-N 0.000 description 1
- QHLQRRCHBRRLTD-UHFFFAOYSA-N 1,2,3,4,5-pentafluoro-6-(2,3,4,5,6-pentafluorophenyl)sulfonylbenzene Chemical class FC1=C(F)C(F)=C(F)C(F)=C1S(=O)(=O)C1=C(F)C(F)=C(F)C(F)=C1F QHLQRRCHBRRLTD-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- YYGLIYSHHLEMBA-UHFFFAOYSA-N 1,3,4,5,6,8,9,10-octafluorophenanthrene-2,7-diamine Chemical compound NC1=C(F)C(F)=C2C3=C(F)C(F)=C(N)C(F)=C3C(F)=C(F)C2=C1F YYGLIYSHHLEMBA-UHFFFAOYSA-N 0.000 description 1
- UPEJSMHLCNUHTI-UHFFFAOYSA-N 1,3,4,5,7,8,9,10-octafluoroanthracene-2,6-diamine Chemical compound FC1=C(N)C(F)=C(F)C2=C(F)C3=C(F)C(N)=C(F)C(F)=C3C(F)=C21 UPEJSMHLCNUHTI-UHFFFAOYSA-N 0.000 description 1
- IUOXPRAKZDRRNN-UHFFFAOYSA-N 1,3,4,5,7,8-hexafluoronaphthalene-2,6-diamine Chemical compound FC1=C(N)C(F)=C(F)C2=C(F)C(N)=C(F)C(F)=C21 IUOXPRAKZDRRNN-UHFFFAOYSA-N 0.000 description 1
- NFOHISGFHBRCDU-UHFFFAOYSA-N 1,3,4,6,8,9-hexafluorothianthrene-2,7-diamine Chemical compound NC1=C(F)C(F)=C2SC3=C(F)C(N)=C(F)C(F)=C3SC2=C1F NFOHISGFHBRCDU-UHFFFAOYSA-N 0.000 description 1
- OTEKOJQFKOIXMU-UHFFFAOYSA-N 1,4-bis(trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=C(C(Cl)(Cl)Cl)C=C1 OTEKOJQFKOIXMU-UHFFFAOYSA-N 0.000 description 1
- KFSRWJOFHDWKBX-UHFFFAOYSA-N 1-n,1-n,2-n,2-n-tetrachlorobenzene-1,2-diamine Chemical compound ClN(Cl)C1=CC=CC=C1N(Cl)Cl KFSRWJOFHDWKBX-UHFFFAOYSA-N 0.000 description 1
- IQLSKIMWFZOTQN-UHFFFAOYSA-N 1-n,1-n,3-n,3-n-tetrachlorobenzene-1,3-diamine Chemical compound ClN(Cl)C1=CC=CC(N(Cl)Cl)=C1 IQLSKIMWFZOTQN-UHFFFAOYSA-N 0.000 description 1
- QJWKKSKFMMETDK-UHFFFAOYSA-N 1-n,1-n,3-n,3-n-tetrafluorobenzene-1,3-diamine Chemical compound FN(F)C1=CC=CC(N(F)F)=C1 QJWKKSKFMMETDK-UHFFFAOYSA-N 0.000 description 1
- GBKZRUCVLTWAML-UHFFFAOYSA-N 2,3,4,5-tetrachloroaniline Chemical compound NC1=CC(Cl)=C(Cl)C(Cl)=C1Cl GBKZRUCVLTWAML-UHFFFAOYSA-N 0.000 description 1
- UNMPTFOVNHEDAA-UHFFFAOYSA-N 2,3,4,6,7,8-hexafluoronaphthalene-1,5-diamine Chemical compound FC1=C(F)C(F)=C2C(N)=C(F)C(F)=C(F)C2=C1N UNMPTFOVNHEDAA-UHFFFAOYSA-N 0.000 description 1
- FXGQUGCFZKMIJW-UHFFFAOYSA-N 2,4,5,6-tetrafluorobenzene-1,3-diamine Chemical compound NC1=C(F)C(N)=C(F)C(F)=C1F FXGQUGCFZKMIJW-UHFFFAOYSA-N 0.000 description 1
- HQCHAOKWWKLXQH-UHFFFAOYSA-N 2,6-Dichloro-para-phenylenediamine Chemical compound NC1=CC(Cl)=C(N)C(Cl)=C1 HQCHAOKWWKLXQH-UHFFFAOYSA-N 0.000 description 1
- CMMCMQMZCCAYMJ-UHFFFAOYSA-N 2,6-diamino-1,3,4,5,7,8,10,10-octafluoroanthracen-9-one Chemical compound FC1=C(N)C(F)=C2C(F)(F)C3=C(F)C(F)=C(N)C(F)=C3C(=O)C2=C1F CMMCMQMZCCAYMJ-UHFFFAOYSA-N 0.000 description 1
- LWMYJRIVGRFYSI-UHFFFAOYSA-N 2,6-diamino-1,3,4,5,7,8-hexafluoroanthracene-9,10-dione Chemical compound NC1=C(F)C(F)=C2C(=O)C3=C(F)C(N)=C(F)C(F)=C3C(=O)C2=C1F LWMYJRIVGRFYSI-UHFFFAOYSA-N 0.000 description 1
- ZQQOGBKIFPCFMJ-UHFFFAOYSA-N 2-(trifluoromethyl)benzene-1,4-diamine Chemical compound NC1=CC=C(N)C(C(F)(F)F)=C1 ZQQOGBKIFPCFMJ-UHFFFAOYSA-N 0.000 description 1
- DBXWYFWABYAIPK-UHFFFAOYSA-N 2-n-(trifluoromethyl)benzene-1,2-diamine Chemical compound NC1=CC=CC=C1NC(F)(F)F DBXWYFWABYAIPK-UHFFFAOYSA-N 0.000 description 1
- PXUAIMCBQXEGKY-UHFFFAOYSA-N 3,4,5-trifluoro-6-(2,3,4,5,6-pentafluorophenyl)benzene-1,2-diamine Chemical group FC1=C(F)C(N)=C(N)C(C=2C(=C(F)C(F)=C(F)C=2F)F)=C1F PXUAIMCBQXEGKY-UHFFFAOYSA-N 0.000 description 1
- AEPRLEOZMILXQA-UHFFFAOYSA-N 3-(4-amino-2,3,5,6-tetrafluorophenyl)-2,4,5,6-tetrafluoroaniline Chemical group FC1=C(F)C(N)=C(F)C(F)=C1C1=C(F)C(N)=C(F)C(F)=C1F AEPRLEOZMILXQA-UHFFFAOYSA-N 0.000 description 1
- JNVPREWJXAKJQM-UHFFFAOYSA-N 4,6-dichloroisoindole-1,3-dione Chemical class ClC1=CC(Cl)=CC2=C1C(=O)NC2=O JNVPREWJXAKJQM-UHFFFAOYSA-N 0.000 description 1
- RQWJHUJJBYMJMN-UHFFFAOYSA-N 4-(trifluoromethyl)benzene-1,2-diamine Chemical compound NC1=CC=C(C(F)(F)F)C=C1N RQWJHUJJBYMJMN-UHFFFAOYSA-N 0.000 description 1
- ZCTYGKMXWWDBCB-UHFFFAOYSA-N 4-(trifluoromethyl)benzene-1,3-diamine Chemical compound NC1=CC=C(C(F)(F)F)C(N)=C1 ZCTYGKMXWWDBCB-UHFFFAOYSA-N 0.000 description 1
- SLBMJVDWNHZWKZ-UHFFFAOYSA-N 4-[4-amino-2,3-difluoro-5-(trifluoromethyl)phenyl]-2,3,5,6-tetrafluoroaniline Chemical group FC(F)(F)C=1C(=C(C(=C(C=1)C1=C(C(=C(C(=C1F)F)N)F)F)F)F)N SLBMJVDWNHZWKZ-UHFFFAOYSA-N 0.000 description 1
- BAFJJKUNTDYHGT-UHFFFAOYSA-N 4-n-(trifluoromethyl)benzene-1,4-diamine Chemical compound NC1=CC=C(NC(F)(F)F)C=C1 BAFJJKUNTDYHGT-UHFFFAOYSA-N 0.000 description 1
- KGOSXXUJPCFKDF-UHFFFAOYSA-N 5-(trifluoromethoxy)benzene-1,3-diamine Chemical compound FC(OC=1C=C(C=C(C=1)N)N)(F)F KGOSXXUJPCFKDF-UHFFFAOYSA-N 0.000 description 1
- KZSXRDLXTFEHJM-UHFFFAOYSA-N 5-(trifluoromethyl)benzene-1,3-diamine Chemical compound NC1=CC(N)=CC(C(F)(F)F)=C1 KZSXRDLXTFEHJM-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 206010013786 Dry skin Diseases 0.000 description 1
- OBATUXBOGJDXGD-UHFFFAOYSA-N FC1=C(C(=C(C(=C1F)F)F)F)C=1C(=C(C=CC=1)C(C)C)C(C)C Chemical class FC1=C(C(=C(C(=C1F)F)F)F)C=1C(=C(C=CC=1)C(C)C)C(C)C OBATUXBOGJDXGD-UHFFFAOYSA-N 0.000 description 1
- UFOYTIUAPCHPQK-UHFFFAOYSA-N FC1=CC=CC=C1.NC=1C=C(C=CC1N)C=CC1=CC=CC=C1 Chemical compound FC1=CC=CC=C1.NC=1C=C(C=CC1N)C=CC1=CC=CC=C1 UFOYTIUAPCHPQK-UHFFFAOYSA-N 0.000 description 1
- WMTSSPTVMOAXGW-UHFFFAOYSA-N NC1=C(C(=C(C(=C1F)F)F)N)C1=C(C(=C(C=C1)F)F)F Chemical group NC1=C(C(=C(C(=C1F)F)F)N)C1=C(C(=C(C=C1)F)F)F WMTSSPTVMOAXGW-UHFFFAOYSA-N 0.000 description 1
- JATZYXVKPMSNKL-UHFFFAOYSA-N NC1=C(F)C(F)=C(C(F)F)C(F)=C1F Chemical compound NC1=C(F)C(F)=C(C(F)F)C(F)=C1F JATZYXVKPMSNKL-UHFFFAOYSA-N 0.000 description 1
- CLDLQZNAPUQPKN-UHFFFAOYSA-N OC(C1=CC=C(C(Cl)=O)C(Cl)=C1C(O)=O)=O Chemical class OC(C1=CC=C(C(Cl)=O)C(Cl)=C1C(O)=O)=O CLDLQZNAPUQPKN-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000001118 alkylidene group Chemical group 0.000 description 1
- 230000009435 amidation Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- VHFZNEZTCRDDHQ-UHFFFAOYSA-N bis(3-amino-2,4,5,6-tetrafluorophenyl)methanone Chemical compound NC1=C(F)C(F)=C(F)C(C(=O)C=2C(=C(F)C(F)=C(N)C=2F)F)=C1F VHFZNEZTCRDDHQ-UHFFFAOYSA-N 0.000 description 1
- WCIQLLFUGPIURI-UHFFFAOYSA-N bis(4-amino-2,3,5,6-tetrafluorophenyl)methanone Chemical compound FC1=C(F)C(N)=C(F)C(F)=C1C(=O)C1=C(F)C(F)=C(N)C(F)=C1F WCIQLLFUGPIURI-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- JDZLOJYSBBLXQD-UHFFFAOYSA-N difluoromethylbenzene Chemical compound FC(F)C1=CC=CC=C1 JDZLOJYSBBLXQD-UHFFFAOYSA-N 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229920001002 functional polymer Polymers 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 1
- 125000005062 perfluorophenyl group Chemical group FC1=C(C(=C(C(=C1F)F)F)F)* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 150000004807 phenyl sulfones Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/14—Polyamide-imides
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B6/00—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings
- G02B6/02—Optical fibres with cladding with or without a coating
- G02B6/02033—Core or cladding made from organic material, e.g. polymeric material
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Optical Fibers, Optical Fiber Cores, And Optical Fiber Bundles (AREA)
Abstract
A polyamideimide for optical communications, having a minimum light absorption loss in a near infrared light wavelength range, high thermal stability and excellent film processibility, and a method for preparing the same are provided. The polyamideimide has a higher refractive index than the conventional fluorinated polyamideimide. Thus, when using such polyamideimide as a material for a core of an optical fiber, the selection range on the material for cladding becomes wide. Also the coating property and adhesiveness to a substrate are improved, thereby providing a good film processibility and heat resistance.
Description
The invention relates to the polyamidoimide and the method for making thereof that are used for optical communication, more particularly, is about the optical communication polyamidoimide of minimum light loss, high thermal stability and good processing film is arranged near infrared wavelength region, and manufacture method.
The light wavelength scope that is used for optical communication moves to 1550nm from 800nm, and this is equivalent near infrared wavelength region.Thereby, preferably produce optical communication device and use the material that absorbs light in the near infrared wavelength region hardly.
Polymkeric substance is usually as optical substrate such as optical lens or CD etc.Nearest many people attempt to use some polymkeric substance like this to be used for light transmission in the near infrared wavelength region as optical waveguide material.
General polymer generally absorbs the light of 1000-1700nm, and this light is equivalent near infrared wavelength region.Polymkeric substance absorbs only being caused by the stretching vibration of carbon-hydrogen (C-H) key and the strong harmonic wave of mistake that deformation vibration is produced in alkyl, phenyl or other similar functions group in the near infrared wavelength region.Thereby, do not wish to use general polymer as utilizing the optical wave-guide materials of the light of near infrared wavelength region, because bigger light loss is arranged.In order to reduce light loss, the light absorption wavelength zone of polymkeric substance needs to move to longer or shorter wavelength region may near infrared wavelength region.In order to reach this purpose, having proposed a kind of method is that the hydrogen in the c h bond is replaced with fluorine (F) or heavy hydrogen (D).
Particularly, under the situation that fluorine is replaced with heavy hydrogen, the C-D key can cause the photoabsorption in the 1500nm wavelength region, thereby the material of optical communication device uses the 1500nm wavelength inapplicable.On the other hand, hydrogen is replaced with fluorine, the optical absorption loss of wavelength in the 1000-1700nm scope can be minimized.
Make optics such as optoelectronic integrated circuit (OEIC), electro-optic hybrid circuit board (OEMWB), mix integrated device, plastic optical fiber or multi-chip module (MGM), must in making processes, have good thermostability, should resist anti-about 250 ℃ temperature especially.Because the thermostability of optical material is very important factor, so must think over second-order transition temperature, heat decomposition temperature, thermal expansivity or the double refraction of optical material.
Polyimide is a kind of polymkeric substance with good thermal stability that is widely known by the people.Because polyimide is stable under about 400 ℃ high temperature,, people use polyimide as the optical communication material so making great efforts research.
Yet, general because common polyimide has many c h bonds on molecular structure, so bigger light loss occurs near infrared region.In order to overcome this problem, a kind of method has been proposed recently, with the hydrogen partial ground on the polyimide c h bond or all replace it with fluorine.
Yet, replaced by fluorine as hydrogen, just the refractive index of polymkeric substance descends.At this moment, the fluorine content in the polymkeric substance just is directly proportional with the decline level of refractive index.Thereby, because the polyimide that hydrogen on c h bond has been replaced by fluorine, that is the polyimide of having fluoridized, low refractive index had, using under the nuclear core situation of this polyimide as optical fiber, the range of choice that can be used as the material of coating layer just becomes very narrow.
And the fluorine content in the polyimide is high more, and the surface tension of composition that then contains polyimide is low more.Thereby be difficult to such composition is applied on the matrix, and the tension force of the film of being made up of this composition is very poor.As a result, the characteristic attenuation of film is broken easily with this film that forms.Thereby, be difficult to of the practical application of this polyimide input as the optical communication material.
In order to address the above problem, the purpose of this invention is to provide some polyamideimides and be used for optical communication, they have minimum light loss in the near infrared wavelength region of 1000-1700nm, at 200 ℃ or above high thermostability and good film processibility arranged.
Another object of the present invention provides the method for making of the polyamidoimide that is used for optical communication, this polyamidoimide has minimum light loss in 1000-1700nm near-infrared wavelength scope, 200 ℃ of temperature or above high thermostability and good processing film arranged.
Correspondingly, for reaching first purpose, the polyamidoimide that provides some to be used for optical communication, promptly with the polyamidoimide that be used for optical communication of the represented monomer of formula (1) as repeating unit:
X in the formula
1, X
2And X
3All be selected from separately as next group: halogen atom, halogenated alkyl group, halo alkoxy group, halo aromatic ring group ,-NO
2,-OR
1With-SR
1(R herein
1Be haloalkyl or halo aromatic ring group), and Z
1And Z
2Be to be selected from: divalence halo virtue aliphatic hydrocarbon, divalence halo alicyclic hydrocarbon or divalence halogenated aromatic as next group.
Best X
1, X
2And X
3Identical and be selected from: chlorine atom, part chlorination or whole fluorinated alkyls, part chlorination or whole chlorination aromatic ring groups, part chlorination or whole kelene oxygen groups, and part chlorination or perchlorizing phenoxy group group as next group.
And, Z
1And Z
2Be to be selected from: divalence halo C as next group
1-C
25Aliphatic hydrocarbon, divalence halo C
1-C
25Alicyclic hydrocarbon, and divalence halo C
1-C
25Aromatic hydrocarbon.Better, Z
1And Z
2Be to be selected from represented one group of following formula:
Perhaps
Y in the formula
1, Y
2, Y
3And Y
4All be selected from separately as next group: halogen atom, halogenated alkyl group, halo alkoxy group, halo aromatic ring group ,-NO
2,-OR
1With-SR
1(R herein
1Be haloalkyl or halo aromatic ring group); And Q is simple chemical bond or is selected from as next group :-O-,-CO-,-SO
2-,-S-,-(OT)
m-,-(TO)
m-and-(OTO)
m-(T is that halo alkylidene group or halo arylidene and m are integers of 1 to 10 herein).
In order to reach second purpose, a kind of method for making that is used for the polyamidoimide of optical communication is provided, this polymeric amide acid amides has with the represented monomer of chemical formula (1) as repeating unit, and its method for making comprises the following step:
(a) will two (3,5,6-trialkyl-4-halogen formyl-1,2-phthalic acid imide) derivatives (A) with diamine compound (B) in-20-50 ℃ reaction, then with reaction mixture with distilled water or a kind of organic solvent deposit, obtain the polymeric amide amido acid; And
(b) imidization of polymeric amide amido acid:
X in the formula
1, X
2And X
3All be selected from separately as next group: halogen atom, haloalkyl, halogenated alkoxy, halo aromatic ring group ,-NO
2,-OR
1And-SR
1(R herein
1Be haloalkyl or halo aromatic ring group), and Z
1Individual Z
2Be to be selected from: divalence halogenated aliphatic hydrocarbon, divalence halo alicyclic hydrocarbon or divalence halogenated aryl hydrocarbon as next group; And Y is a halogen atom.
Be preferably in the step (a), two (3,5,6-trialkyl-4-halogen formyl radical-1,2-Phthalimide) derivative (A) reacted 100-230 hour at 5-20 ℃ with diamine compound (B).
The polymeric amide amido acid carries out imidization reaction and can be undertaken by chemical process or thermology method in step (b).In chemical process, the polymeric amide amido acid mixes with diacetyl oxide and pyridine, yet 60-150 ℃ of heating, or toluene is joined in the polymeric amide amido acid and is heated to then the boiling point of toluene.In thermology method, preferably the polymeric amide amido acid is heated by several steps in 50-400 ℃ temperature range.
Polyamidoimide of the present invention has higher refractive index than common fluoro polyimide.If this polyamidoimide as the nuclear core, is just had various selections to coating layer material.And some problems that produced in common fluorinated polyimide, that is the low tackiness that produces owing to low surface tension and to the relatively poor coating performance of matrix all can be resolved.
In polyamidoimide of the present invention because-OH and-the strong harmonic wave of mistake of CH and near infrared wavelength region, particularly the photoabsorption that produces in the 1000-1700nm scope that is equivalent to the optical communication wavelength region can be minimized.Because the light loss that causes of C-Cl key absorb light is lower than C-F key, to be used for the optical communication field be of great use as the optical waveguides polymkeric substance so have the polyamidoimide of C-Cl key.Though polyamidoimide of the present invention, in the optical communication wavelength region because-the strong harmonic wave of mistake of NH key also may produce some optical absorption loss, yet in its molecule, only exist limited quantity-this polyamidoimide of NH key, compare with common polyimide, aspect double refraction and thermal expansion, is a kind of good optical material because the flexible molecule structure is arranged.
In polyamidoimide of the present invention, the hydrogen of c h bond is replaced by halogen atom or nitro.Halogen atom replaces the H atom herein, is not limited to a certain specific halogen atom, and various halogen atom to combine be possible.
Below the method for making of polyamidoimide will be described according to the present invention.
The method of two (3,5,6-trialkyl-4-halogen formyl-1, the 2-Phthalimide) derivatives (A) of preparation is described with reference to reaction formula (1).
With 1 (C) and a kind of halogenated compound such as hydrogen bromide, hydrogenchloride or hydrogen fluoride, or with a kind of nitration reaction agent such as nitric acid, one reacts, preparation 3,5,6-trialkyl-1 (D).
With 3,5,6-trialkyl-1 (D) utilizes transition-metal catalyst, potassium permanganate or nitric acid etc. to carry out oxidation by various method for oxidation, obtains 3,5,6-trialkyl-1,2,4-benzene tricarbonic acid (E).
With 3,5,6-trialkyl-1,2,4-benzene tricarbonic acid (E) and acetate and acetic anhydride prepare 3,5,6-trialkyl-4-carboxylic acid-1,2-phthalate anhydride (F), and react with diamine compound (B '), prepare two (3,5,6-trialkyl-4-carboxylic acid-1,2-Phthalimide) derivative (G).
Two (3,5,6-trialkyl-4-carboxylic acid-1,2-Phthalimide) derivative (G) reacts with a kind of halogenated compound such as thionyl chloride, prepares two (3,5,6-trialkyl-4-halogen formyl-1,2-Phthalimide) derivatives (A).
At reaction formula (1), X
1, X
2And X
3Each is selected from separately as next group: halogen atom, haloalkyl, halogenated alkoxy, halo aromatic ring group ,-NO
2,-OR
1With-SR
1(R herein
1Be haloalkyl or halo aromatic ring group), Z
1Be to be selected from the divalence halogenated aliphatic hydrocarbon, divalence halo alicyclic hydrocarbon or divalence halogenated aryl hydrocarbon, and Y is a halogen atom.
The synthesis condition of above-mentioned two (3,5,6-trialkyl-4-halogen formyl-1,2-Phthalimide) derivatives (A) is described in detail in detail now.
1 and iodine are dissolved in the chloroform, and to wherein adding a kind of halogenated compound such as hydrogen bromide, hydrogenchloride or hydrogen fluoride, perhaps nitrating agent such as nitric acid reacted 15 minutes to 24 hours at 0-40 ℃ then tempestuously.Throw out in the reaction mixture is filtered, obtain 3,5,6-trialkyl-1.
To 3,5, add pyridine and water in 6-trialkyl-1, and 100 ℃ of heating, to wherein adding potassium permanganate and reacting 2-24 hour at 50-115 ℃.When reaction mixture is still warm, filter, under vacuum, distill then to remove in the pyridine reaction mixture.
In reagent, add entry and sodium hydroxide,,, reacted then 2 to 24 hours to wherein adding potassium permanganate then 50-100 ℃ of heating.With the reaction mixture that obtains 5N-HCl solution acidifying, boil off solvent then subsequently, obtain 3,5,6-trialkyl benzene-1,2,4-tricarboxylic acid.
To 3,5,6-trialkyl benzene-1,2 adds halogenated compound such as thionyl chloride in the 4-tricarboxylic acid, reacted 30 minutes to 24 hours, obtains 3,5,6-trialkyl-4-carboxylic acid-1,2-phthalate anhydride.
With 3,5,6-trialkyl-4-carboxylic acid-phthalate anhydride and a kind of diamine compound (B ') were 0-200 ℃ of reaction 4 to 48 hours.
The product that obtains is precipitated in distilled water or in organic solvent such as the methyl alcohol, filter, drying obtains two (3,5,6-trialkyl-4-carboxylic acid-1,2-Phthalimide) derivatives (G).
This derivative (G) and a kind of halogenated compound such as thionyl chloride be 0-50 ℃ of reaction, and 80-100 ℃ of heating 24 to 72 hours, make two (3,5,6-trialkyl-4-halogen formyl-1,2-Phthalimide) derivatives (A).
Will two (3,5,6-trialkyl-4-halogen formyl radical-1,2-Phthalimide) derivatives (A) be dissolved in and make in the polar solvent-20-50 ℃ reaction 2 to 300 hours with a kind of diamine compound (B).Here can use N as polar solvent, dinethylformamide, N,N-dimethylacetamide, N, N-dimethyl sulfoxide (DMSO) or N-N-methyl-2-2-pyrrolidone N-.
Reaction mixture is precipitated in distilled water or in organic solvent such as the methyl alcohol, and form the polymeric amide amido acid, promptly a kind of intermediate.Again the polymeric amide amido acid is carried out imidization with the preparation polyamidoimide.
Available chemical process or thermology method carry out imide reaction with the polymeric amide amido acid and generate polyamidoimide.
In chemical process, be that diacetyl oxide and pyridine are joined in the mixture that contains two (3,5,6-trialkyl-4-halogen formyl radical-1,2-Phthalimide) derivatives (A) and diamine compound (B), and 60-150 ℃ of heating.In addition, also toluene can be joined in the mixture that contains two (3,5,6-three alkane-4-halogen formyl radical-1,2-Phthalimide) derivatives (A) and diamine compound (B), and be heated to the boiling point of toluene.In thermology method, be that the polymeric amide amido acid is heated through several steps in 50-400 ℃ temperature range.
Be understandable that the polymeric amide amido acid carries out amidation and becomes polyamidoimide, be with thermogravimetic analysis (TGA) (TGA) method 200-250 ℃ of measurement, its thermolysis is to betide 300-500 ℃, particularly at 375-425 ℃.
With the resulting polyamidoimide of the present invention of aforesaid method, have second-order transition temperature being 220-320 ℃ is 1 * 10 with molecular weight
4-5 * 10
5Dalton.The molecular weight of polyamidoimide is measured with gel permeation chromatography (GPC).
Diamine compound B and B ' are not limited to a certain specific compound.Diamine compound (B) is not limited to a certain specific compound.For example diamine compound (B) and (B ') can be two (perfluorophenyl) alkanes, two (perfluorophenyl) sulfone class, two (perfluorophenyl) ethers or α-α '-two (perfluorophenyl) diisopropyl benzene class.In detail, diamine compound (B) comprises tetrafluoro-1, the 2-phenylenediamine, tetrafluoro-1,3-phenylenediamine, tetrafluoro-1, the 4-phenylenediamine, tetrachloro-1,2-phenylenediamine, tetrachloro-1,3-phenylenediamine, tetrachloro-1, the 4-phenylenediamine, hexafluoro-1,5-diaminonaphthalene, hexafluoro-2,6-diaminonaphthalene, 3-trifluoromethyl three fluoro-1, the 2-phenylenediamine, 4-trifluoromethyl three fluoro-1,2-phenylenediamine, 2-trifluoromethyl three fluoro-1,3-phenylenediamine, 4-trifluoromethyl three fluoro-1, the 3-phenylenediamine, 5-trifluoromethyl three fluoro-1,3-phenylenediamine, 2-trifluoromethyl three fluoro-1,4-phenylenediamine, 3-pentafluoroethyl group three fluoro-1, the 2-phenylenediamine, 4-pentafluoroethyl group three fluoro-1,2-phenylenediamine, 2-pentafluoroethyl group three fluoro-1,3-phenylenediamine, 4-pentafluoroethyl group three fluoro-1, the 3-phenylenediamine, 5-pentafluoroethyl group three fluoro-1,3-phenylenediamine, 2-pentafluoroethyl group three fluoro-1,4-phenylenediamine, 3, two (trifluoromethyl) two fluoro-1 of 4-, 2-phenylenediamine, 3, two (trifluoromethyl) two fluoro-1 of 5-, 2-phenylenediamine, 2, two (trifluoromethyl) two fluoro-1 of 4-, 3-phenylenediamine, 4, two (trifluoroethyl) two fluoro-1 of 5-, 3-phenylenediamine, 2, two (trifluoromethyl) two fluoro-1 of 3-, 4-phenylenediamine, 2, two (trifluoromethyl) two fluoro-1 of 5-, 4-phenylenediamine, 3, two (trifluoromethyl) two fluoro-1 of 4-, 2-phenylenediamine, 3-trifluoromethoxy three fluoro-1, the 2-phenylenediamine, 4-trifluoromethoxy three fluoro-1,2-phenylenediamine, 2-trifluoromethoxy three fluoro-1,3-phenylenediamine, 4-trifluoromethoxy three fluoro-1, the 3-phenylenediamine, 5-trifluoromethoxy-1,3-phenylenediamine, 2-trifluoromethoxy-1, the 4-phenylenediamine, 3,4, three (trifluoromethyl) fluoro-1 of 5-, the 2-phenylenediamine, 3,4, three (trifluoromethyl) fluoro-1 of 6-, the 2-phenylenediamine, 2,4, three (trifluoromethyl) fluoro-1 of 5-, the 3-phenylenediamine, 2,4, three (trifluoromethyl) fluoro-1 of 6-, the 3-phenylenediamine, 4,5, three (trifluoromethyl) fluoro-1 of 6-, the 3-phenylenediamine, four (trifluoromethyl)-1,2-phenylenediamine, four (trifluoromethyl)-1, the 3-phenylenediamine, four (trifluoromethyl)-1,4-phenylenediamine, 3,3 '-diamino octafluoro biphenyl, 3,4 ' diamino octafluoro biphenyl, 4,4 '-diamino octafluoro biphenyl, 3,3 '-diamino octafluoro biphenyl, 3,4 ' diamino, eight chlordiphenyls, 4,4 '-diamino eight chlordiphenyls, 2,2 '-two (trichloromethyl)-4,4 '-diamino chlordene biphenyl, 3,3 '-two (trichloromethyl)-4,4 '-diamino chlordene biphenyl, two (the amino tetrafluoro phenyl of 4-) methylene dichloride, 1,2-two (the amino tetrafluoro phenyl of 4-) tetrachloroethane, 2,2-two (the amino tetrafluoro phenyl of 4-) chlordene propane, 2,2 '-two (trifluoromethyl)-4,4 '-diamino chlordene biphenyl, 3,3 '-two (trifluoromethyl)-4,4 '-diamino hexafluoro biphenyl, two (the amino tetrafluoro phenyl of 4-) methylene fluoride, 1,2-two (the amino tetrafluoro phenyl of 4-) tetrachloroethane, 2,2-two (the amino tetrafluoro phenyl of 4-) HFC-236fa, two (the amino tetrafluoro phenyl of 3-) ether, 3,4-diamino octafluoro phenyl ether, two (the amino tetrafluoro phenyl of 4-) ether, two (the amino tetrachloro phenyl of 3-) ether, 3,4 '-diamino eight chlorodiphenyl ethers, two (the amino tetrachloro phenyl of 4-) ether, 3,3 '-diamino octafluoro benzophenone, 3,4 '-diamino octafluoro benzophenone, 4,4 '-diamino octafluoro benzophenone, two (the amino tetrafluoro phenyl of 3-) sulfone, 3,4 '-diamino octafluoro sulfobenzide, two (the amino tetrafluoro phenylsulfones of 4-), two (the amino tetrafluoro phenyl of 3-) thioether, 3,4 '-diamino octafluoro diphenyl sulfide, two (the amino tetrafluoro phenyl of 4-) thioether, the amino tetrafluoro phenoxy group-4 of 4-'-amino tetrafluoro phenyl methylene fluoride, two (the amino tetrafluoro phenoxy group of 4-) methylene fluoride, 1,2-two (the amino tetrafluoro phenoxy group of 4-) Tetrafluoroethane, 2,2-two (the amino tetrafluoro phenoxy group of 4-) HFC-236fa, two (the amino tetrafluoro phenoxy group of 4-) ethylene dichloride, 1,2-two (the amino tetrafluoro phenoxy group of 4-) tetrachloroethane, 2,2-two (the amino tetrafluoro phenoxy group of 4-) chlordene propane, 4,4 " diamino 12 fluoro-right-terphenyl; 2 '; 3 '-two (trifluoromethyl) 4,4 " diamino-right-terphenyl, 2,2 " two (trifluoromethyl)-4; 4 "-diamino-right-terphenyl, 2 ' 5 '-two (trifluoromethyl)-4,4 " diamino-right-terphenyl; 2; 7-diamino hexafluoro diphenylene-oxide, 1,4-two (the amino tetrafluoro phenoxy group of 4-) tetra fluoro benzene; 2; 6-diamino hexafluoro naphthalene, 2,7-diamino octafluoro phenanthrene; 2,6-diamino octafluoro anthracene, 2,7-diamino hexafluoro thianthrene, 2,6-diamino hexafluoro anthraquinone, 2,6-diamino hexafluoro biphenyl, 2,6-diamino octafluoro anthrone, 2,7-diamino tetrafluoro hexichol [b, e] 1, the 4-diox, 2,2 '-two (4-aminophenyl) HFC-236fa, 2,2 '-two (4-aminophenyl) chlordene propane, 2,4-diamino benzo trifluoride, 2, two (trifluoromethyl) p-diaminodiphenyl of 2-, 2, two [4-(4-amino-2-trifluoromethoxy phenoxy base) phenyl] HFC-236fa of 2-, 2, two [4-(4-amino-2-trifluoromethoxy phenoxy base) phenyl] the chlordene propane of 2-, 3,4-diamino benzo trifluoride, 3,5-diamino benzo trifluoride, 2,5-diamino benzo trifluoride, 2, two [4-(4-amino-benzene oxygen) phenyl] HFC-236fa of 2-, 2, two [4-(4-amino-benzene oxygen) phenyl] the chlordene propane of 2-, perhaps 3,4-diaminostilbene-fluorobenzene.
To be described in detail the present invention by some embodiment below.But the invention is not restricted to following these embodiment.Synthetic embodiment 1
With 0.008 mole 3,5,6-three chloro-4-chloroformyl phthalic acids are in 50 ℃ of N-N-methyl-2-2-pyrrolidone N-s that are dissolved in 50ml, the temperature with reaction mixture is reduced to room temperature then.
In this reaction mixture, add 0.04 mole 1, the 3-diaminobenzene at room temperature reacted 6 hours then.Subsequently reaction mixture was reacted 4 hours at 180 ℃.
After reaction is finished, reaction mixture is joined in the distilled water, form throw out.The throw out that obtains is filtered and drying.In 0.0038 mole products therefrom, add 0.15 mole thionyl chloride and 0.0076 mole pyridine.
With reaction mixture 0-50 ℃ of reaction: then reaction mixture is distilled under vacuum removing solvent wherein, and several times with distilled water wash.With the product that obtains in 80 ° baking oven dry 24 hours, obtain two [three chloro-4-chlorobenzene dicarboximide derivatives (BTHP) (1) (yields: synthetic embodiment 2 92%) then
With 0.008 mole 3,5,6-three chloro-4-chloroformyl phthalate anhydrides are dissolved in 50 milliliters the N-N-methyl-2-2-pyrrolidone N-at 50 ℃, the temperature with reaction mixture is reduced to room temperature then.In reaction mixture, add 0.04 mole 4,4 '-benzidine, at room temperature reacted then 5 hours.Subsequently reaction mixture was reacted 4 hours at 180 ℃.
After reaction is finished, reaction mixture is joined in the distilled water, form throw out.The product that obtains is filtered and drying.
In 0.0038 mole products therefrom, add 0.15 mole thionyl chloride and 0.0076 mole pyridine.
With reaction mixture 0-50 ℃ of reaction.Then reaction mixture is distilled under vacuum, removing solvent wherein, and with distilled water wash several times.Then with the product that obtains in vacuum drying oven 80 ℃ of dryings 24 hours, obtain BTHP (2) (yield: 87%).Synthetic embodiment 3
With 0.008 mole 3,5,6-three chloro-4-chloroformyl phthalate anhydrides are dissolved under 50 ℃ in 50 milliliters the N-N-methyl-2-2-pyrrolidone N-, the temperature with reaction mixture is reduced to room temperature then.
In reaction mixture, add 0.04 mole 1,3-diamino tetra fluoro benzene is then room temperature reaction 5 hours.Subsequently reaction mixture was reacted 4 hours at 180 ℃.
After reaction is finished, reaction mixture is joined in the distilled water, form throw out.The throw out that obtains is filtered and drying.
The pyridine of 0.15 mole thionyl chloride and 0.0076 mole joined in 0.0038 mole the products therefrom.
With in the reaction mixture 0-50 ℃ of reaction.Then reaction mixture is distilled under vacuum to remove solvent and several times wherein with distilled water wash.Then that the product that obtains is dry in being set at 80 ℃ vacuum drying oven, obtain BTHP (3) (yield: 86%).Synthetic embodiment 4
With 0.008 mole 3,5,6-three chloro-4-chloroformyl phthalate anhydrides are dissolved in 50 milliliters of N-N-methyl-2-2-pyrrolidone N-s at 50 ℃, the temperature with reaction mixture is reduced to room temperature then.
With 0.04 mole 4,4 '-diamino octafluoro biphenyl joins in this reaction mixture, then room temperature reaction 5 hours.Subsequently reaction mixture was reacted 4 hours at 180 ℃.After reaction is finished, reaction mixture is joined in the distilled water, make the formation throw out.The throw out that obtains is filtered and drying.
The pyridine of 0.15 mole thionyl chloride and 0.0076 mole joined in 0.0038 mole the products therefrom.
With reaction mixture 0-50 ℃ of reaction.Then reaction mixture is distilled under vacuum to remove solvent and several times wherein with distilled water wash.With products therefrom in being set at 80 ℃ vacuum drying oven dry 24 hours, obtain BTHP (4) (yield: 80%).Synthetic embodiment 5
With 0.008 mole 3,5,6-three chloro-4-chloroformyl phthalate anhydrides are dissolved in 50 milliliters of N-methyl-2-pyridine alkane ketone of 50 ℃, the temperature with reaction mixture is reduced to room temperature then.
With 0.04 mole 2, two (4-aminophenyl) propane of 2-join in the reaction mixture, at room temperature react then 5 hours.Subsequently reaction mixture was reacted 4 hours at 180 ℃.
After reaction is finished, reaction mixture is joined in the distilled water, form throw out.The throw out that obtains is filtered and drying.
The pyridine of 0.15 mole thionyl chloride and 0.0076 mole joined in 0.0038 mole the products therefrom.
With reaction mixture 0-50 ℃ of heating.Then, reaction mixture is distilled under vacuum to remove solvent and several times wherein with distilled water wash.With the product that obtains in being set at 80 ℃ vacuum drying oven dry 24 hours, obtain BTHP (5) (yield: 85%) then.Synthetic embodiment 6
With 0.008 mole 3,5,6-three chloro-4-chloroformyl phthalate anhydrides are dissolved in 50 milliliters of N-N-methyl-2-2-pyrrolidone N-s of 50 ℃, the temperature with reaction mixture is reduced to room temperature then.
With 0.04 mole 2, two (4-aminophenyl) the chlordene propane of 2-join in the reaction mixture, then room temperature reaction 5 hours.Subsequently reaction mixture was reacted 4 hours at 180 ℃.
After reaction is finished, reaction mixture joined make the formation throw out in the distilled water, the throw out that obtains is filtered and dry.
The pyridine of 0.15 mole thionyl chloride and 0.0078 mole joined in 0.0038 mole the products therefrom.
With reaction mixture 0-50 ℃ of reaction.Then reaction mixture is distilled under vacuum to remove solvent and several times wherein with distilled water wash.With products therefrom in being set at 80 ℃ vacuum drying oven dry 24 hours, obtain BTHP (6) (yield: 82%) then.Synthetic embodiment 7
With 0.008 mole 3,5,6-three chloro-4-chloroformyl phthalate anhydrides are dissolved in 50 ℃ 50 milliliters the N-N-methyl-2-2-pyrrolidone N-, the temperature with reaction mixture is reduced to room temperature then.
With 0.04 mole 2,2 '-two (4-amino tetrafluoro phenyl) chlordene propane joins in the reaction mixture, at room temperature reacted then 5 hours.Subsequently reaction mixture was reacted 4 hours at 180 ℃.
After reaction is finished, reaction mixture is joined in the distilled water, make the formation throw out.The throw out of gained is filtered and drying.
The pyridine of 0.15 mole thionyl chloride and 0.0076 mole joined in 0.0038 mole the products therefrom.
With reaction mixture 0-50 ℃ of reaction.Then reaction mixture is distilled under vacuum to remove solvent and several times wherein with distilled water wash.With the product that obtains in being set at 80 ℃ vacuum drying oven dry 24 hours, obtain BTHP (7) (yield: 81%) then.Synthetic embodiment 8
With 0.008 mole 3,5,6-three chloro-4-chloroformyl phthalate anhydrides are dissolved in 50 milliliters of N-methyl-2-pyridine alkane ketone of 50 ℃, the temperature with reaction mixture is reduced to room temperature then.
With 0.04 mole 2,2 '-two (4-amino tetrafluoro phenyl) hexafluoro biphenyl joins in the reaction mixture, at room temperature reacted then 5 hours.Subsequently reaction mixture was reacted 4 hours at 180 ℃.
After reaction is finished, reaction mixture joined make the formation throw out in the distilled water.The throw out that obtains is filtered and drying.
The pyridine of 0.15 mole thionyl chloride and 0.0076 mole joined in 0.0038 mole the products therefrom.
With reaction mixture 0-50 ℃ of reaction.Then reaction mixture is distilled under vacuum to remove solvent and several times wherein with distilled water wash.With the product that obtains in being set at 80 ℃ vacuum drying oven dry 24 hours, obtain BTHP (8) (yield: 78%) then.Synthetic embodiment 9
With 0.008 mole 3,5,6-three chloro-4-chloroformyl phthalate anhydrides are dissolved in 50 milliliters N-methyl-2-pyridine alkane ketone of 50 ℃, the temperature of reaction mixture is reduced to room temperature then.
Two (4-aminophenyl) ethers of 0.04 mole are joined in the reaction mixture, at room temperature reacted then 5 hours.Subsequently reaction mixture was reacted 4 hours at 180 ℃.
After reaction is finished, reaction mixture joined make the formation throw out in the distilled water.Throw out is filtered and drying.
The pyridine of 0.15 mole thionyl chloride and 0.0076 mole joined in 0.0038 mole the products therefrom.
With reaction mixture 0-50 ℃ of reaction.Then reaction mixture is distilled under vacuum to remove solvent and several times wherein with distilled water wash.With products therefrom in being set at 80 ℃ vacuum drying oven dry 24 hours, obtain BTHP (9) (yield: 81%) then.Synthetic embodiment 10
With 0.008 mole 3,5,6-three chloro-4-chloroformyl phthalate anhydrides are dissolved in 50 milliliters of N-N-methyl-2-2-pyrrolidone N-s of 50 ℃, the temperature with reaction mixture is reduced to room temperature then.
Two (the amino tetrachloro phenyl of 4-) ether with 0.04 mole joins in the reaction mixture, at room temperature reacts then 5 hours.Subsequently reaction mixture was reacted 4 hours at 180 ℃.
After reaction is finished, reaction mixture joined make the formation throw out in the distilled water, the throw out that obtains is filtered and dry.
The pyridine of 0.15 mole thionyl chloride and 0.0076 mole joined in 0.0038 mole the products therefrom.
With reaction mixture 0-50 ℃ of reaction.Then reaction mixture is distilled under vacuum to remove solvent and several times wherein with distilled water wash.With products therefrom in being set at 80 ℃ vacuum drying oven dry 24 hours, obtain BTHP (10) (yield: 79%) then.Synthetic embodiment 11
With 0.008 mole 3,5,6-three chloro-4-chloroformyl phthalate anhydrides are dissolved in 50 milliliters of N-N-methyl-2-2-pyrrolidone N-s of 50 ℃, the temperature with reaction mixture is reduced to room temperature then.
Two (the amino tetrafluoro phenyl of 4-) sulfone of 0.04 mole is joined in the reaction mixture, at room temperature reacted then 5 hours.Subsequently reaction mixture was reacted 4 hours at 180 ℃.
After reaction is finished, reaction mixture joined make the formation throw out in the distilled water.With sedimentation and filtration and the drying that obtains.
The pyridine of 0.15 mole thionyl chloride and 0.0076 mole joined in 0.0038 mole the products therefrom.
With reaction mixture 0-50 ℃ of reaction.Then reaction mixture is distilled under vacuum to remove solvent and several times wherein with distilled water wash.With products therefrom in being set at 80 ℃ vacuum drying oven dry 24 hours, obtain BTHP (11) (yield: 75%) then.Synthetic embodiment 12
With 0.008 mole 3,5,6-three chloro-4-chloroformyl phthalate anhydrides are dissolved in 50 ℃ 50 milliliters the N-N-methyl-2-2-pyrrolidone N-, the temperature with reaction mixture is reduced to room temperature then.
With 0.04 mole 2,2 '-two (trifluoromethyl) p-diaminodiphenyl joins in the reaction mixture, then room temperature reaction 5 hours.Subsequently reaction mixture was reacted 4 hours at 180 ℃.
After reaction is finished, reaction mixture joined make the formation throw out in the distilled water.The throw out that obtains is filtered and drying.
The pyridine of 0.15 mole thionyl chloride and 0.0076 mole joined in 0.0038 mole the reaction product.
With reaction mixture 0-50 ℃ of reaction.Then reaction mixture is distilled under vacuum to remove solvent and several times wherein with distilled water wash.With the product that obtains in being set at 80 ℃ vacuum drying oven dry 24 hours, obtain BTHP (12) (yield: 76%) then.Synthetic embodiment 13
With 0.008 mole 3,5,6-three chloro-4-chloroformyl phthalate anhydrides are dissolved in 50 ℃ 50 milliliters the N-N-methyl-2-2-pyrrolidone N-, the temperature with reaction mixture is reduced to room temperature then.
Two (the amino tetrafluoro phenyl of 4-) methylene fluoride of 0.04 mole is joined in the reaction mixture, at room temperature reacted then 5 hours.Subsequently reaction mixture was reacted 4 hours at 180 ℃.
After reaction is finished, reaction mixture joined make the formation throw out in the distilled water, the throw out that obtains is filtered and dry.
The pyridine of 0.15 mole thionyl chloride and 0.0076 mole joined in 0.0038 mole the reaction product.
With reaction mixture 0-50 ℃ of reaction.Then reaction mixture is distilled under vacuum removing solvent wherein, and with distilled water wash several times.With the product that obtains in being set at 80 ℃ vacuum drying oven dry 24 hours, obtain BTHP (13) (yield: 73%) then.
Embodiment 1
To contain 0.001 mole 1, the 3-phenylene two (3,5,6-three chloro-4-chloroformyl Phthalimide, 0.001 mole 1, the mixture of 3-diaminobenzene and 3 milliliters of N,N-dimethylacetamide at room temperature with nitrogen in reaction 9 days.
Reaction mixture joined make the formation throw out in the distilled water.With throw out filter and several times with distilled water wash.
Then with products therefrom in being set at 60 ℃ vacuum drying oven dry 24 hours, and be heated to 250 ℃, just obtain polyamidoimide (PAI) (1) (yield: 91%).
Embodiment 2
To contain 0.001 mole 1, the 3-phenylene two (3,5,6-three chloro-4-chloroformyl Phthalimide, 0.001 mole 4,4 '-mixture of benzidine and 4 milliliters of N,N-dimethylacetamide reacted 7 days under room temperature and nitrogen.
Reaction mixture joined make the formation throw out in the distilled water.With throw out filter and several times with distilled water wash.
Then with products therefrom in being set at 60 ℃ vacuum drying oven dry 24 hours, and be heated to 250 ℃, obtain PAI (2) (yield: 88%).
Embodiment 3
To contain 0.001 mole 2,4,5,6-tetrafluoro phenylene-1,3-two (3,5,6-three chloro-4-chloroformyl Phthalimide), 0.001 mole 1, the mixture of 3-diamino tetra fluoro benzene and 5 milliliters of N,N-dimethylacetamide, reaction is 9 days under room temperature and nitrogen.
Reaction mixture joined make the formation throw out in the distilled water.With throw out filter and several times with distilled water wash.
Then with products therefrom in being set at 60 ℃ vacuum drying oven dry 24 hours, and to wherein adding diacetyl oxide and pyridine, and heating.
Reaction mixture joined make the formation throw out in the distilled water.The throw out that obtains filtered and several times with distilled water wash.
With the product that obtains in being set at 60 ℃ vacuum drying oven dry 24 hours, obtain PAI (3) (yield: 86%).
Embodiment 4
To contain 0.001 mole octafluoro xenyl-4,4 '-two (3,5,6-three chloro-4-chloroformyl Phthalimide), 0.001 mole 4,4 '-mixture of diamino octafluoro biphenyl and 3 milliliters of N,N-dimethylacetamide reacted 9 days under room temperature and nitrogen.
Reaction mixture joined make the formation throw out in the distilled water.With throw out filter and several times with distilled water wash.
With products therefrom in being set at 60 ℃ vacuum drying oven dry 24 hours and diacetyl oxide and pyridine joined wherein, and heat it.
Reaction mixture joined make the formation throw out in the distilled water.The throw out that obtains filtered and several times with distilled water wash.
With products therefrom in being set at 60 ℃ vacuum drying oven dry 24 hours, obtain PAI (4) (yield: 83%).Embodiment 5
To contain 0.001 mole octafluoro xenyl-4,4 '-two (3,5,6-three chloro-4-chloroformyl Phthalimide), 0.001 mole two (4-aminophenyl) methane and the mixture of 4 milliliters of N,N-dimethylacetamide, reaction is 9 days under room temperature and nitrogen.
Reaction mixture joined make the formation throw out in the distilled water.The throw out that obtains filtered and several times with distilled water wash.
Then with products therefrom in being set at 60 ℃ vacuum drying oven dry 24 hours, and be heated to 250 ℃, obtain PAI (5) (yield: 81%).
Embodiment 6
To contain 0.001 mole 1,3-chlordene isopropylidene-2,2-phenylbenzene two (3; 5; 6-three chloro-4-chloroformyl Phthalimide), the mixture of two (4-amino-tetrafluoro phenyl) methylene fluoride of 0.001 mole and 5 milliliters of N,N-dimethylacetamide at room temperature reacted 9 days down with nitrogen.
Reaction mixture joined make the formation throw out in the distilled water.The throw out that obtains filtered and several times with distilled water wash.
Be added on wherein then with the product that obtains in being set at 60 ℃ vacuum drying oven dry 24 hours, and with diacetyl oxide and pyridine, reheat it.
Reaction mixture joined make the formation throw out in the distilled water, the throw out that obtains is filtered and several times with distilled water wash.
With the product that obtains in being set at 60 ℃ vacuum drying oven dry 24 hours, obtain polyamidoimide PAI (6) (yield: 78%).
Embodiment 7
To contain 0.001 mole 1,3-chlordene isopropylidene-2,2-xenyl two (3; 5,6-three chloro-4-chloroformyl Phthalimide), 0.001 mole 2; the mixture of two (4-aminophenyl) propane of 2-and 3 milliliters of N,N-dimethylacetamide, reaction is 9 days under room temperature and nitrogen.
Reaction mixture joined make the formation throw out in the distilled water.The throw out that obtains filtered and several times with distilled water wash.
Then with the product that obtains in being predefined for 60 ℃ vacuum drying oven dry 24 hours, and to wherein adding diacetyl oxide and pyridine, reheat it.
Reaction mixture joined make the formation throw out in the distilled water.And the throw out that obtains filtered and several times with distilled water wash.
With products therefrom in being predefined for 60 ℃ vacuum drying oven dry 24 hours, obtain PAI (7) (yield: 81%).
Embodiment 8
To contain 0.001 mole 1; 3-chlordene isopropylidene-2; 2-octafluoro xenyl-4; 4 '-two (3; 5,6-three chloro-4-chloroformyl Phthalimide), 0.001 mole 2; the mixture of two (4-aminophenyl) the chlordene propane of 2-and 4 milliliters of N,N-dimethylacetamide reacted 9 days under room temperature and nitrogen.
Reaction mixture joined make the formation throw out in the distilled water.The throw out that obtains filtered and several times with distilled water wash.
Then with the product that obtains in being predefined for 60 ℃ vacuum drying oven dry 24 hours, and be heated to 250 ℃, obtain PAI (8) (yield: 76%).
Embodiment 9
To contain 0.001 mole 1; 3-chlordene isopropylidene-2; 2-octafluoro xenyl-4; 4 '-two (3; 5,6-three chloro-4-chloroformyl Phthalimide), 0.001 mole 2; the mixture of two (the amino tetrafluoro phenyl of the 4-) HFC-236fa of 2-and 3 milliliters of N,N-dimethylacetamide at room temperature reacted 9 days down with nitrogen.
Reaction mixture joined make the formation throw out in the distilled water.The throw out that obtains filtered and several times with distilled water wash.
With resulting product in being predefined for 60 ℃ vacuum drying oven dry 24 hours, and be heated to 250 ℃, obtain PAI (9) (yield: 73%).
Embodiment 10
To contain 0.001 mole 4,4 '-eight chlorodiphenyl ethers two (3,5; 6-three chloro-4-chloroformyl Phthalimide); 0.001 2 of mole, the mixture of two (4-tetrafluoro phenyl) the chlordene propane of 2-and 5 milliliters of N,N-dimethylacetamide reacted 9 days under room temperature and nitrogen.
Reaction mixture joined make the formation throw out in the distilled water.The throw out that obtains filtered and several times with distilled water wash.
Then with products therefrom in predetermined 60 ℃ vacuum drying oven dry 24 hours, and be heated to 250 ℃, obtain PAI (10) (yield: 74%).
Embodiment 11
To contain 0.001 mole 4,4 '-eight chlorodiphenyl ethers two (3,5,6-three chloro-4-chloroformyl Phthalimide), 0.001 mole two (4-aminophenyl) ethers and the mixture of 5 milliliters of N,N-dimethylacetamide reacted 9 days under room temperature and nitrogen.
Reaction mixture joined make the formation throw out in the distilled water.The throw out that obtains filtered and several times with distilled water wash.
Then,, and be heated to 250 ℃, obtain PAI (11) (yield: 85%) products therefrom in being predefined for 60 ℃ vacuum drying oven dry 24 hours.
Embodiment 12
To contain 0.001 mole 4,4 '-eight chlorodiphenyl ethers two (3,5,6-three chloro-4-chloroformyl Phthalimide), 0.001 mole two (the amino tetrachlorobenzene of the 4-) ethers and the mixture of 5 milliliters of N,N-dimethylacetamide reacted 9 days under room temperature and nitrogen.
Reaction mixture joined make the formation throw out in the distilled water.The throw out that obtains filtered and several times with distilled water wash.
Then, with products therefrom in being predefined for 60 ℃ vacuum drying oven dry 24 hours, and to wherein adding diacetyl oxide and pyridine, and heating.
Reaction mixture joined make the formation throw out in the distilled water.The throw out that obtains filtered and several times with distilled water wash.
With products therefrom in being set at 60 ℃ vacuum drying oven dry 24 hours, obtain PAI (12) (yield: 74%).
After measured thermostability, light loss the near infrared wavelength region of 1000-1700nm in and the film processing properties of 1 to 12 synthetic of embodiment (1) to each polyamidoimide PAI of (12).
The thermostability of these polyamidoimides is to have done measurement with thermogravimetic analysis (TGA) (TGA) method.
As a result, true 350-450 ℃ thermolysis test according to PAI 1 to 12, as can be seen, the thermostability of these polyamidoimides is good.
And, to observe, the light loss of this polyamidoimide is similar to or is less than common perfluorination polyamidoimide.
Also have, during contrast, common partially fluorinated or perfluorination polyimide have relatively poor processing film, and compare with common polyimide by the polyamideimides that embodiment 1 to 12 obtains, have the film processing properties of having improved.
Polyamidoimide of the present invention has higher refractive index than common fluorinated polyimide.Thereby, when using this polymeric amide acid amides, the range of choice of coating layer with material broadened as fibre-optic nuclear core material.And, to compare with common polyimide, polyamidoimide of the present invention is improved to the coating performance and the bond properties of matrix, provides good film processibility and thermostability with this.
And, owing to polyamidoimide of the present invention can be minimized the light loss of near infrared wavelength region, so polyamidoimide of the present invention is of great use as the optical material in near-infrared wavelength optical communication field.That is, polyamidoimide of the present invention, can be used as functional polymer material with low light absorption loss characteristic, and low light absorption is lost characteristic for production optical waveguides optics device such as optoelectronic integrated circuit (OEIC), electro-optic hybrid circuit board (OEMWB), and it is essential mixing integrated device, multi-chip module (MCM) or plastic optical fiber etc.
Claims (11)
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| KR1019970082004A KR100490444B1 (en) | 1997-12-31 | 1997-12-31 | Polyamide-imide for Optical Communication |
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| CNB981117937A Expired - Lifetime CN1138818C (en) | 1997-12-31 | 1998-12-30 | Polyamideimide for optical communications and method for preparing the same |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6028159A (en) |
| JP (1) | JP2994373B2 (en) |
| KR (1) | KR100490444B1 (en) |
| CN (1) | CN1138818C (en) |
| DE (1) | DE19860845B4 (en) |
| GB (1) | GB2332910B (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI304076B (en) * | 2001-07-13 | 2008-12-11 | Nippon Catalytic Chem Ind | |
| GB2388228A (en) * | 2002-05-02 | 2003-11-05 | Mark Richard Goode | A vehicle immobiliser system combined with a road tax, MOT and insurance payment system |
| KR20150083837A (en) | 2012-10-17 | 2015-07-20 | 브로민 콤파운드 리미티드 | Process for the polymerization of pentabromobenzyl (meth) acrylate, the polymer obtained and uses thereof |
| CN104181072B (en) * | 2014-08-12 | 2016-07-27 | 黑龙江省科学院高技术研究院 | A kind of method utilizing thermogravimetic analysis (TGA) method to determine polyamide acid film hot imidization technique |
| US11220480B2 (en) | 2016-12-31 | 2022-01-11 | Shpp Global Technologies B.V. | Synthesis of reactive intermediates for polyetherimides, and uses thereof |
| WO2023192255A1 (en) * | 2022-03-30 | 2023-10-05 | Zymergen Inc. | Optically transparent polyamide-imides |
| WO2023211747A1 (en) * | 2022-04-29 | 2023-11-02 | Zymergen Inc. | Optically transparent polyamideimide |
| CN119296867A (en) * | 2024-12-11 | 2025-01-10 | 佳腾电业(赣州)股份有限公司 | Insulated wire, preparation method thereof, coil and electronic/electric equipment |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4377652A (en) * | 1978-02-17 | 1983-03-22 | Asahi Kasei Kogyo Kabushiki Kaisha | Polyamide-imide compositions and articles for electrical use prepared therefrom |
| JP2842535B2 (en) * | 1988-07-25 | 1999-01-06 | 三菱化学株式会社 | Aromatic polyamideimide |
| US5233018A (en) * | 1990-09-28 | 1993-08-03 | Nippon Telegraph And Telephone Corporation | Perfluorinated polyimide, perfluorinated poly(amic acid), starting compounds therefor, and methods for preparing them |
| JP2886348B2 (en) * | 1990-12-27 | 1999-04-26 | 三井化学株式会社 | Method for producing polyamide-imide resin |
| JP2912711B2 (en) * | 1990-12-28 | 1999-06-28 | 三井化学株式会社 | Method for producing polyamide-imide resin |
| US5187254A (en) * | 1991-05-31 | 1993-02-16 | Amoco Corporation | Amide-imide resin having phthalic anhydride moieties |
| US5266679A (en) * | 1991-08-30 | 1993-11-30 | Eastman Kodak Company | Method for producing polyamide-imides from CO, bis-imide and polyamine |
| KR0128814B1 (en) * | 1993-07-05 | 1998-04-07 | 강박광 | Novel polyamideimide resins containing isophoronediamine structures |
| KR970006897B1 (en) * | 1993-11-12 | 1997-04-30 | 재단법인 한국화학연구소 | The method of polyamide imide pesin |
| BE1008499A3 (en) * | 1994-07-11 | 1996-05-07 | Dsm Nv | Polyamideimide. |
| KR0161313B1 (en) * | 1994-10-31 | 1999-01-15 | 강박광 | Polyimide amicester and process for preparing the same |
| KR100283949B1 (en) * | 1997-12-08 | 2001-03-02 | 윤종용 | Polyamideimide for optical communication and manufacturing method therof |
-
1997
- 1997-12-31 KR KR1019970082004A patent/KR100490444B1/en not_active IP Right Cessation
-
1998
- 1998-12-30 CN CNB981117937A patent/CN1138818C/en not_active Expired - Lifetime
- 1998-12-31 US US09/223,728 patent/US6028159A/en not_active Expired - Lifetime
- 1998-12-31 DE DE19860845A patent/DE19860845B4/en not_active Expired - Fee Related
- 1998-12-31 GB GB9828862A patent/GB2332910B/en not_active Expired - Fee Related
-
1999
- 1999-01-04 JP JP11000229A patent/JP2994373B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CN1226571A (en) | 1999-08-25 |
| GB2332910A (en) | 1999-07-07 |
| JPH11255897A (en) | 1999-09-21 |
| GB2332910B (en) | 2000-03-08 |
| DE19860845A1 (en) | 1999-07-08 |
| KR100490444B1 (en) | 2005-09-02 |
| GB9828862D0 (en) | 1999-02-17 |
| JP2994373B2 (en) | 1999-12-27 |
| KR19990061714A (en) | 1999-07-26 |
| US6028159A (en) | 2000-02-22 |
| DE19860845B4 (en) | 2006-10-26 |
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